Diaper Christopher M, Goldring William P D, Pattenden Gerald
School of Chemistry, The University of Nottingham, University Park, Nottingham, UK NG7 2RD.
Org Biomol Chem. 2003 Nov 21;1(22):3949-56. doi: 10.1039/b307986d.
A total synthesis of the PAF antagonist phomactin A (1), isolated from the marine fungus Phoma sp. is described. The synthesis is based on a Cr(II)/Ni(II) macrocyclisation from the aldehyde vinyl iodide 14, leading to the key phomactatrienol intermediate 16a, followed by elaboration of 16a to the epoxyketone 21, which undergoes spontaneous pyran and hemiacetal ring formation to 1 on deprotection with DDQ.
